2-Chloromethyl 2-(trimethylsilyl)ethyl ether → 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole

HRID 467548

反応式

HRID 467548 の反応式
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.[CH3:15][Si:16]([CH3:23])([CH3:22])[CH2:17][CH2:18][O:19][CH2:20]Cl>CN1C(=O)CCC1>[CH3:1][C:2]1([CH3:14])[C:6]([CH3:7])([CH3:8])[O:5][B:4]([C:9]2[CH:13]=[N:12][N:11]([CH2:20][O:19][CH2:18][CH2:17][Si:16]([CH3:23])([CH3:22])[CH3:15])[CH:10]=2)[O:3]1

参加物

4

反応物 2

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

生成物 1

HCID 574776664-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (8.2 g, 41 mmol) in NMP (60 mL) was added K2 CO3 (12 g, 82 mmol) and 2-(trimethylsilyl)ethoxymethyl chloride (7.8 mL, 43 mmol) in sequence. The reaction mixture was stirred at r.t. under N2 for 16 h. Then, the reaction mixture was diluted and filtered, and then the filtrate was diluted with EtOAc (300 mL). The resulting solution was washed with sat. NaHCO3 (aq) (3×200 mL), H2O (4×200 mL), brine (1×200 mL), dried over Na2SO4, filtered, concentrated and dried in vacuo to yield intermediate Int-15a (11.4 g, 86%) as a clear yellowish oil.

後処理

  1. additionThen, the reaction mixture was diluted
  2. filtrationfiltered
  3. additionthe filtrate was diluted with EtOAc (300 mL)
  4. washThe resulting solution was washed with sat. NaHCO3 (aq) (3×200 mL), H2O (4×200 mL), brine (1×200 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried in vacuo
  9. customto yield intermediate Int-15a (11.4 g, 86%) as a clear yellowish oil

出典と根拠

ORDレコード
ord-24b076b08e6141dc8d360f7e8d15dcd4
出典データセット
uspto-grants-2014_01
特許番号
US08623857B2

関連ノート

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